Structure-activity relationships of adenine and deazaadenine derivatives as ligands for adenine receptors, a new purinergic receptor family.

Adenine derivatives bearing substituents in the 2-, N(6)-, 7-, 8-, and/or 9-position and a series of deazapurines were synthesized and investigated in [(3)H]adenine binding studies at the adenine receptor in rat brain cortical membrane preparations (rAde1R). Steep structure-activity relationships were observed. Substitution in the 8-position (amino, dimethylamino, piperidinyl, piperazinyl) or in the 9-position (2-morpholinoethyl) with basic residues or introduction of polar substituents at the 6-amino function (hydroxy, amino, acetyl) represented the best modifications.

8-Chloro-7-(2,6-dichlorobenzyl)-1,3-dimethyl-7H-purine-2,6(1H,3H)-dione.

The title compound, C14H11Cl3N4O2, consists of two planar fragments which are nearly perpendicular to one another. The crystal packing is controlled by intra- and intermolecular C-H..